1,4-Diacryloylpiperazine

Details:

1,4-Diacryloylpiperazine is a chemical compound with the molecular formula C??H??N?O?, widely used in polymer chemistry and materials science. Below is a breakdown of its properties, applications, and safety considerations:

1. Chemical Structure & Properties

• Structure:

  • A piperazine ring (a six-membered ring with two nitrogen atoms at positions 1 and 4) substituted with acryloyl groups (–CO–CH?–CH?) on both nitrogen atoms.

  • Functional groups: Two reactive acrylate groups (vinyl groups), enabling polymerization.

• Key Properties:

  • Crosslinking Agent: Acts as a bifunctional monomer (two reactive sites), forming covalent bonds in polymer networks.

  • Thermal Stability: Stable under standard conditions but polymerizes upon exposure to heat, light, or initiators (e.g., UV light, peroxides).

  • Solubility: Typically soluble in polar organic solvents (e.g., DMF, DMSO) but insoluble in water.

2. Primary Applications

(1) Polymer Chemistry

• Hydrogel Synthesis:
  Used to create crosslinked hydrogels for biomedical applications (e.g., drug delivery, wound dressings, tissue engineering).

  • Example: Combined with acrylamide or polyethylene glycol (PEG) to form biocompatible networks.

• Coatings & Adhesives:
  Enhances mechanical strength and durability in UV-curable resins, adhesives, or 3D printing materials.

• Chromatography Resins:
  Serves as a crosslinker in affinity chromatography media for protein purification.

(2) Biomedical Research

• Drug Delivery Systems:
  Crosslinked polymers control drug release rates by tuning hydrogel porosity.

• Bioconjugation:
  Reacts with biomolecules (e.g., proteins, peptides) via Michael addition or radical reactions.

(3) Cosmetics

• Nail Polishes & Hair Gels:
  Provides structural integrity in long-lasting formulations.

3. Safety & Handling

• Hazards:

  • Skin/Eye Irritant: Acrylates can cause sensitization or allergic reactions.

  • Respiratory Risks: Inhalation of dust/particulates may irritate mucous membranes.

• Precautions:

  • Use PPE (gloves, goggles, lab coat).

  • Work in a fume hood to avoid inhalation.

  • Store in a cool, dark place to prevent polymerization.

4. Commercial Availability

• Suppliers:
  Available from chemical suppliers like Sigma-Aldrich, TCI Chemicals, or Alfa Aesar.

• Synonyms:

  • N,N'-Diacryloylpiperazine

  • *1,4-Bis(acryloyl)piperazine*

Key Takeaway

1,4-Diacryloylpiperazine is a versatile crosslinker critical for designing advanced polymeric materials, especially in biomedical and industrial applications. Its reactivity requires careful handling but offers flexibility in tailoring material properties like elasticity, porosity, and biocompatibility.